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41541

Sigma-Aldrich

1,8-Bis(tetramethylguanidino)naphthalene

≥98.0%

Synonym(s):

N′′,N′′′′′-1,8-Naphthalenediylbis(N,N,N′,N′-tetramethyl-guanidine), TMGN

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About This Item

Linear Formula:
C10H6[N=C[N(CH3)2]2]2
CAS Number:
442873-72-5
Molecular Weight:
354.49
MDL number:
MFCD06798180
UNSPSC Code:
12352100
PubChem Substance ID:
57650064
NACRES:
NA.22

Assay

≥98.0%

impurities

≤0.5% water

mp

124-128 °C

solubility

toluene: 20 mg/mL, clear

SMILES string

CN(C)\C(=N\c1cccc2cccc(\N=C(\N(C)C)N(C)C)c12)N(C)C

InChI

1S/C20H30N6/c1-23(2)19(24(3)4)21-16-13-9-11-15-12-10-14-17(18(15)16)22-20(25(5)6)26(7)8/h9-14H,1-8H3

InChI key

PSHHYQWGIGYWHP-UHFFFAOYSA-N

Related Categories

Analysis Note

may contain dark particles

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Borislav Kovacević et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 8(7), 1694-1702 (2002-04-05)
The spatial and electronic structure of the very strong neutral organic bases bis(tetramethylguanidino)naphthalene (TMGN), 4,5-bis(tetramethylguanidino)fluorene (TMGF) and some related compounds are explored by ab initio computational methods. Their affinity towards the proton is scrutinized both in the gas phase and
Volker Raab et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 8(7), 1682-1693 (2002-04-05)
1,8-Bis(tetramethylguanidino)naphthalene (TMGN, 1) is a new, readily accessible, and stable "proton sponge" with an experimental pK(BH(+)) value of 25.1 in MeCN, which is nearly seven orders of magnitude higher in basicity than the classical proton sponge 1,8-bis(dimethylamino)-naphthalene (DMAN). Because of
Strong Organic Bases as Building Blocks of Mesoporous Hybrid Catalysts for C-C Forming Bond Reactions.
Gianotti E, et al.
European Journal of Inorganic Chemistry, 32, 5175-5185 (2012)
Dong Cao et al.
Talanta, 85(1), 345-352 (2011-06-08)
Determination of perfluorinated compounds (PFCs) is very important because of their potential hazards to the environment and human health. In present work, 1,8-bis (tetramethylguanidino)-naphthalene (TMGN), a superbasic proton sponge, was firstly employed as the matrix for quantitative detection of acidic
Dong Cao et al.
The Analyst, 137(9), 2218-2225 (2012-03-22)
1,8-Bis(dimethylamino)naphthalene (DMAN), a classical 'proton sponge', was functionalized on silica particles as a novel solid-phase extraction (SPE) adsorbent (DMAN@silica) for extracting perfluoroalkyl sulfonates (PFSs). High reproducibility and excellent extraction capability for PFSs were obtained in a wide pH range (3.0~8.5).

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